Chloride → 3-Phenoxybenzaldehyde

HRID 2398116Notes

Reaction equation

HRID 2398116 reaction equation
N1C=CC=CC=1.[Cl-].[O:8]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18][OH:19])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl.[O-2].[O-2].[O-2].[Cr+6]>[O:8]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[O:19])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 312ChlorideHCID 1049PyridineHCID 262953-Phenoxybenzyl alcohol

Product 1

HCID 382843-Phenoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

Chromium trioxide (3.00 g.) was added to a stirred solution of pyridine (4.75 g.) in dry methalene chloride (75 ml.), and stirring was continued for a further 15 minutes. 3-Phenoxybenzyl alcohol (1 g.) in methylene chloride (5 ml.) was added, the mixture stirred for a further 15 minutes, decanted and the residue washed with diethyl ether (100 ml.). The filtrate was washed with 55 sodium hydroxide solution (3 × 50 ml), 2.5 NHCl (50 ml.) and 5% sodium carbonate solution (50 ml.) and dried over Na2SO4 to give 3-phenoxy-benzaldehyde. Alternatively the alcohol can be oxidized using Jones' reagent, a similar yield of aldehyde being obtained. Yield (0.80 g.), b.p. 126°/0.8 mm.Hg, nD = 1.5984.

Workup

  1. stirringthe mixture stirred for a further 15 minutes
  2. customdecanted
  3. washthe residue washed with diethyl ether (100 ml.)
  4. washThe filtrate was washed with 55 sodium hydroxide solution (3 × 50 ml), 2.5 NHCl (50 ml.) and 5% sodium carbonate solution (50 ml.)
  5. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-d71c269b158d4cbc9e2f94fc7698466b
Source dataset
uspto-grants-1977_05
Patent number
US04024163

Reaction notes

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